How to Find out Anything from Anyone

A former intelligence officer shares interrogation tips for getting people to spill on first dates and their salaries

Wish you knew whether the wisecracking guy in the next cubicle got a raise this year? Or whether that stylish woman sipping wine on your first date wants to have kids? Bet you’d like to know whether your nanny really takes the baby outside everyday per your instructions. Well, a new book by an army intelligence interrogator could help you get the answers to your most pressing questions.

“Find Out Anything from Anyone, Anytime: Secrets of Calculated Questioning From a Veteran Interrogator” by James O. Pyle and Maryann Karinch won’t help you force a hostile to reveal state secrets, but it does suggest ways to turn someone who’s on the fence into spilling what you want to know.

“There are two things people will not give you for free: money and information,” says Pyle, who plied his craft in the U.S. Army, the Army Intelligence Center and School and the Joint Intelligence of the Pentagon. He explains in the book that the key to pulling out information lies in things like the “control” question, in which you ask something to which you already know the answer to find out whether the person is “lying, uninformed, and/or not paying attention,” he says. Then there’s the “persistent” question in which you ask the same thing in different ways to “explore all facets of the desired information.”

But the most important thing to remember is that there’s nothing better at clamming people up than an interrogation. So try not to make it obvious that you’re pumping someone for information, but “have a conversation with information in it,” he says. That means offering up stuff about yourself and showing curiosity and interest in what the other person is saying.

Here’s how this army intelligence expert would help you get an answer in these typical scenarios:

Does a first date want kids?

This is a delicate subject to broach on a first date, and a direct question could scare off many people. Generally, the best approach is to say something about yourself and watch the other person’s reaction. If you want to know, for example, whether he’s been married, you might say that you have been and then watch the response you get. “The eyes are the big tellers,” Pyle says. “Do they say Ohmygosh? Is there a pull back?” Compare that to how the other person looks when talking about non-personal or non-emotional subjects.

For the kid question, he suggests using the “third party” approach. If there’s a child anywhere nearby, you might comment, “Wow, look at that cute kid.” The answer might not be definitive, but you will get very suggestive clues from “I guess, but they don’t belong in fancy restaurants,” versus “I have two little girls and I sure miss them.”

Is my co-worker making more than me?

Asking right out about another person’s salary can seem intrusive, even aggressive. But starting a conversation—and including some sly flattery—might work wonders. “If I was half as good as you are,” you might say, “I’d be earning twice what I’m making.” If your target bites, she might offer something you can build on, such as, “Oh, I’m not making all that much.” Then you could counter with a really high figure. “Oh, you must be making at least X grand.” That’s likely to be met with a disclaimer, “Oh, no, not that much.” Then, Pyle suggests you guess a way-low figure, and she’ll probably respond, “Oh, more than that.” At this point, she may just tell you. But even if she doesn’t, you’ll have a pretty good idea of the answer.

Does the nanny follow my instructions for taking care of my child?

This is a tricky situation. If your nanny did not follow your instructions to take baby Lindsey out, for example, she’ll be very reluctant to tell you. This is where it comes in handy to know the different kinds of questions. Don’t ask a question that produces a yes or no reply, Pyle says. Instead, you might ask these other kinds of questions, always in a conversational way. Ask for a narrative. “How was your walk today? Where did you go? What did you do?” People who want to cover something, according to FBI narrative analysis, tend to minimize and dismiss: “Fine. Just walked around and came back.”
If that’s the response you get, dig in. What time did you go out? What did you see? Who did you meet? If want to check her truthfulness, you can summarize what she’s said and either leave something out or add something in. If she doesn’t catch it and correct you, that’s a sign she may be lying. Also, if you catch her in a contradiction, you can question her further. And if you think she’s just getting flustered, you can relax the tension by asking her a non-pertinent question like “Oh, that smells good; what did you make for dinner?” Then after a while, you can return to the questions you want answered.

What’s the state of my elderly parents finances and how much will I have to pitch in if they need long term care?

Many elderly people are extremely private about their money and won’t tell their kids how much they’ve got, where it is, or whether they’ve signed any documents to allow access in an emergency. For this situation, Pyle advises a different strategy. “Make an appeal,” he says. Express your love and gratitude to them, bring up an example like the neighbor who had a stroke but whose rehab was delayed because she hadn’t given anyone her power of attorney. Then, say, ” I want to ask you some questions, not because I’m nosy, but so you can tell me how I can help you if you need it. ” Then just launch into your questions.

“It’s a disarming approach,” Pyle says. “If they don’t buy it, then ask, “Why can’t we talk about this? Why else?” That may get a useful dialogue going.

In any situation, Pyle says, from asking your 5-year-old what he ate for lunch at school to asking a prisoner of war what he was doing on that road, persistence tends to pay off. He suggests you just keep asking, “What else?” until they say, That’s all.” Most of all, start a conversation in which people want to tell you what you want to know — and likely won’t even realize they’re revealing anything. “You can lead a horse to water, but you can’t make it drink,” he says, adding. “But if you make ’em thirsty, they’ll drink by themselves.”

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